The invention herein described was made in the course of or under a contract thereunder with the United States Air Force Systems Command.
This invention relates to mixtures resulting from the hydrogenolysis of "Binor-S". More particularly the invention relates to mixtures of hexacyclics and pentacyclics and other compounds resulting from the hydrogenolysis of Binor-S, a C.sub.14 heptacyclic saturated hydrocarbon.
It is an object of present invention to provide novel compositions of hexacyclics and pentacyclics and other compounds which compositions are characterized by low freezing points, low melting points and be relatively high net heats of combustion. Said compositions have utility as a high energy fuel which can be used in either jet or rocket propulsion. Jet propulsion includes a jet engine which can be used for a missile plane and others and includes the three basic types, i.e., ramjet, turbo-jet and pulse jet. The term jet generally refers to a device requiring air whereas rocket generally refers to a device containing its own oxygen.
It is also an object of present invention to provide a novel method for preparing the foregoing novel compositions. It is also an object to provide a controlled reaction so that the amount of various components of the novel composition can be varied substantially. Another object is the hydrogenolysis of Binor-S at high conversions (&gt;95%).
Preparation of Binor-S is disclosed in JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 88:21, November 5, 1966, pages 4890-4894, title of article ".pi. Complex Multicenter Reactions Promoted by Binuclear Catalyst Systems". "Binor-S a New Heptacyclotetradecane via Stereospecific Dimerization of Bicycloheptadiene", by G. N. Schrauzer, B. N. Bastian and G. A. Fosselius. Same article also discloses hydrogenation of Binor-S over Pt at 200.degree. C and 4600 p.s.i. Products of the hydrogenation are reported as C.sub.14 H.sub.20 (94 %) and C.sub.14 H.sub.18 (6 %). Binor-S is known by its chemical name of endo,cis,endo-heptacyclo [5.3.1.1.sup.2,6.1.sup.4,12.1.sup.9,11.0.sup.3,5.0.sup.8,10 ]tetradecane. It's melting point is about 65.degree. C. Binor-S can be depicted by the following structural formula: ##STR1##
Binor-S is a C.sub.14 H.sub.16 hydrocarbon containing seven rings and a C/H atomic ratio of 0.875.
Preparation of dimers of bicycloheptadiene is disclosed in U.S. Pat. No. 3,326,993 issued June 20, 1967. The latter discloses that a mixture of bicycloheptadiene dimers has utility as high energy fuel.
Hydrogenation of the foregoing bicycloheptadiene dimers improves its stability towards autoxidation thereby enhancing its utility as a fuel. Such hydrogenated dimers of bicyloheptadiene, in which crystallization has been produced by maintaining at -110.degree. F. (-78.9.degree. C.), are completely melted only by warming to +25.degree. F. (-3.9.degree. C.). The rather high melting point of the last crystalline material of said dimer can hinder its fluid flow at low ambient temperatures.
In contrast, applicants' product, which has been induced to crystallize by maintaining for a prolonged period at -110.degree. F. (78.9.degree. C.), is completely melted on warming to -45.degree. F. (-42.8.degree. C.).